Cyclohexyl isocyanate → HCID 67385304, compound

HRID 906003Notes

Reaction equation

HRID 906003 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([NH2:11])[N:9]=2)[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:3]=1.[CH:20]1([N:26]=[C:27]=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>ClCCCl>[CH:20]1([NH:26][C:27]([NH:11][C:8]2[N:9]=[C:10]3[C:2]([Cl:1])=[CH:3][N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]3=[N:6][CH:7]=2)=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanate2×HCID 67385653HCID 67385653, compound

Product 1

HCID 67385304HCID 67385304, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

7-Chloro-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamine (100 mg, 0.335 mmol) was dissolved in 1,2-dichloroethane (3.4 mL). Cyclohexylisocyanate (0.43 mL, 3.35 mmol) was added and the reaction mixture was heated to reflux overnight, cooled to RT, and concentrated. The residue was dispersed in 3 mL of toluene, cyclohexylisocyanate (0.86 mL, 6.70 mmol) was added and the reaction mixture was heated to reflux overnight, and cooled to 0° C. The precipitates were filtered, washed with toluene and dried under high vacuum to give 44 mg of 1-cyclohexyl-3-[7-chloro-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea as a white solid (31% yield).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. additionThe residue was dispersed in 3 mL of toluene
  5. temperaturethe reaction mixture was heated
  6. temperatureto reflux overnight
  7. temperaturecooled to 0° C
  8. filtrationThe precipitates were filtered
  9. washwashed with toluene
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-0bb8ff0e6e134aaebdbf04d0cb70e15f
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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